5-Bromo-4-cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine → 4-Cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine

HRID 238245노트

반응식

HRID 238245 반응식
Br[C:2]1[C:3]([O:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[N:4][C:5]([CH:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)[CH3:9])=[N:6][CH:7]=1>C(O)C.[Pt]>[CH:28]1([O:27][C:3]2[CH:2]=[CH:7][N:6]=[C:5]([CH:8]([N:10]3[CH2:15][CH2:14][N:13]([S:16]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=4)(=[O:17])=[O:18])[CH2:12][CH2:11]3)[CH3:9])[N:4]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1

참가 물질

4

반응물 1

HCID 599932605-Bromo-4-cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine

생성물 1

HCID 599931654-Cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 702Ethanol용매

실험 절차

To a solution of 5-Bromo-4-cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine (30.0 g, 0.06 mmol) in ethanol (10 ml) was added 10 mg platinum on carbon (0.5% wt). The solution was degassing three times and the hydrogen gas was introduced through a hydrogen balloon. The reaction was heated to reflux for 18 hours at room temperature. The solution was filtrated through a celite column and the solvent was evaporated. Water (5 ml) was then added to the solution and the mixture was extracted with dichloromethane (10 ml). The organic layer was then washed with 10% sodium bisulfite solution, and then washed with saturated brine (2×30 ml). The combined organic phase was collected and dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield a brown crude product. The resulting residue was purified by silica gel chromatography with 50% dichloromethane in hexane. The product was collected and was dried under reduced pressure to give the 4-Cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine (Yield 15 mg, 60%. 1HNMR (400 MHz, CDCl3): δ 1.60-1.54 (m, 2H), 1.64 (d, J=6.82 Hz, 3H), 1.76-1.67 (m, 4H), 1.96-1.84 (m, 2H), 3.35-3.12 (m, 4H), 3.50-3.35 (m, 2H), 3.05 (s, 3H), 4.41 (q, 1H, J=13.64, 7.33 Hz), 5.38 (m, 1H), 6.60 (d, J=5.81, 1H), 6.94 (d, J=8.84, 2H), 7.56 (d, J=8.84, 2H), 8.32 (d, J=5.81, 1H). MS m/z calc. 446.2 found (ESI); 447.2 (M+1)+. Retention time 2.76 minutes.

후처리

  1. customThe solution was degassing three times
  2. additionthe hydrogen gas was introduced through a hydrogen balloon
  3. temperatureThe reaction was heated
  4. filtrationThe solution was filtrated through a celite column
  5. customthe solvent was evaporated
  6. additionWater (5 ml) was then added to the solution
  7. extractionthe mixture was extracted with dichloromethane (10 ml)
  8. washThe organic layer was then washed with 10% sodium bisulfite solution
  9. washwashed with saturated brine (2×30 ml)
  10. customThe combined organic phase was collected
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customto yield a brown crude product
  15. customThe resulting residue was purified by silica gel chromatography with 50% dichloromethane in hexane
  16. customThe product was collected
  17. customwas dried under reduced pressure

출처 및 근거

ORD 기록
ord-d58ec5b9d5ac4381bfe24c7d8b2f4203
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642609B2

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